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US 2006/0217382 A1Published application
Imidazotriazine compounds
AssigneeSmithKline Beecham Corporation
InventorsMui Cheung, Nigel King, Kevin Kuntz, Robert Mook, Mark Pobanz, James Salovich, Brian Wilson
Life of this patent
Estimating the term…
Abstract
The present invention provides compounds of formula (I): wherein all variables are as defined herein, pharmaceutical compositions containing the same, processes for preparing the same and their use as pharmaceutical agents.
Claims37
A compound of formula (I):
- wherein:
- R1 is alkyl;
- w is 0 or 1;
- R11 is H or C1-3alkyl;
- Ring A is selected from the group consisting of cycloalkyl, cycloalkenyl, aryl, 5-13 membered heterocycle and 5-13 membered heteroaryl;
- Ring B is selected from the group consisting of cycloalkyl, cycloalkenyl, aryl, 5-13 membered heterocycle and 5-13 membered heteroaryl;
- a, b, c, f, g, and h are the same or different and are each independently 0 or 1;
- d and j are the same or different and are independently 1 or 2;
- each R2 is the same or different and is independently selected from the group consisting of alkylene, alkenylene and alkynylene;
- Y1 and Y2 are the same or different and are each independently selected from the group consisting of —O—, —S(O)q— and —N(R5)—;
- q is 0, 1 or 2;
- each R3 and R4 are the same or different and are each independently selected from the group consisting of H, halo, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, Ph, Het, —COR5, —CSR5, —CO2R5, —COPh, —CO2Ph, —C(O)Het, —C(O)NR5R6, —C(S)NR5R6, —C(═NR5)R6, —C(═NR5)NR5R6, —CR5═N—OR6, —OR5, —OCOR5, —S(O)pR5, —S(O)2OH, —S(O)pNR5R6, —NR5R6, —NR5COR6, —NR5CO2R6, —NR5SO2R6, —NO2, —CN, —SCN and —N3;
- each p is the same or different and is 0, 1 or 2;
- m and n are the same or different and are each independently 0, 1, 2, 3, 4 or 5;
- each R5 and each R6 are the same or different and are each independently selected from the group consisting of H, alkyl, alkenyl, alkynyl, cycloalkyl and cycloalkenyl;
- Ph is phenyl optionally substituted by one or more substituents selected from the group consisting of halo, alkyl, —CO2R5, —OR5, —SO2R5, —SO2NR5R6, —NR5R6, —R2—(NR5R6)CO2R5, Het, —R2-Het, —CN and —N3;
- and
- Het is a monocyclic 5-6 membered heterocycle or heteroaryl group containing 1, 2 or 3 heteroatoms selected from the group consisting of N, O and S optionally substituted by one or more substituents selected from the group consisting of halo, alkyl, —CO2R5, —C(O)NR5R6, —OR5, —SO2R5, —SO2NR5R6, —NR5R6, oxo, —CN and —N3;
- or a pharmaceutically acceptable salt, solvate or physiologically functional derivative thereof.
16 more elements
A compound selected from the group consisting of:
- 5-Methyl-7-phenyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-7-(2-nitrophenyl)-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 7-(2-Bromophenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 7-(4-Fluorophenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-7-[3-(trifluoromethyl)phenyl]-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 2,2-Dimethyl-N-(2-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}phenyl)propanamide;
- 2,2,2-Trifluoro-N-(2-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}phenyl)acetamide;
- 3-{5-Methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}benzonitrile;
- 7-(3-Bromophenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 7-(3-Bromothien-2-yl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 7-(5-Bromopyridin-3-yl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo-[5,1-f][1,2,4]triazin-2-amine;
- Methyl 3-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}benzoate;
- 7-(5-Bromothien-2-yl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 7-(3-Bromophenyl)-N-[5-(ethylsulfonyl)-2-methoxyphenyl]-5-methylimidazo[5,1-f][1,2,4]triazin-2-amine;
- 7-(3-Bromophenyl)-N-(3-chloro-4-morpholin-4-ylphenyl)-5-methylimidazo[5,1-f][1,2,4]triazin-2-amine;
- 3-{5-Methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}benzamide;
- (2E)-3-(3-{5-Methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}phenyl)prop-2-enamide;
- 5-Methyl-N-(4-nitrophenyl)-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine;
- 2-{3-[(5-Methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-yl)amino]phenyl}ethanol;
- 4-[(5-Methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-yl)amino]benzene-sulfonamide;
- 7-(2-Methoxyphenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 2-{5-Methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}phenol;
- 2-{5-Methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}phenyl acetate;
- 5-Methyl-7-[4-(trifluoromethyl)phenyl]-N-(3,4,5-trimethoxyphenyl)-imidazo[5,1-f][1,2,4]triazin-2-amine;
- N-Methyl-N-{4-[(5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-yl)amino]phenyl}urea;
- 5-Methyl-7-phenyl-N-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine;
- (3-{5-Methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}phenyl)(phenyl)methanone;
- 7-(1,3-Benzodioxol-5-yl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo-[5,1-f][1,2,4]triazin-2-amine;
- Methyl 4-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}benzoate;
- 5-Methyl-7-(3-phenoxyphenyl)-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 7-(3-Aminophenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 7-(1H-Indol-2-yl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-7-(5-nitro-1H-pyrrol-2-yl)-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-7-(1-methyl-1H-pyrrol-2-yl)-N-(3,4,5-trimethoxyphenyl)-imidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-7-( 1-methyl-1H-indol-3-yl)-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 7-(3-Furyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 7-(1H-Indol-5-yl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 2-[(2-{5-Methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}phenyl)thio]benzonitrile;
- 5-Methyl-7-(2-{[3-(trifluoromethyl)phenyl]amino}phenyl)-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-7-quinolin-8-yl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 3-({5-Methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)benzenesulfonamide;
- N-Methyl-N-[4-({5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)phenyl]urea;
- N-[4-Methoxy-3-({5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)phenyl]acetamide;
- 2-[3-({5-Methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)phenyl]ethanol;
- 4-({5-Methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)benzenesulfonamide;
- N-[4-({5-Methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)phenyl]acetamide;
- N-[3-({5-Methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)phenyl]acetamide;
- tert-Butyl 3-({5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)benzylcarbamate;
- 4-({5-Methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)phenol;
- 5-Methyl-N-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-7-[3-(trifluoromethyl)phenyl]-imidazo[5,1-f][1,2,4]triazin-2-amine;
- N-(5-Fluoro-2-methoxyphenyl)-5-methyl-7-[3-(trifluoromethyl)phenyl]-imidazo[5,1-f][1,2,4]triazin-2-amine;
- N-{2-[4-Methoxy-3-({5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)phenyl]ethyl}acetamide;
- N-[5-(2-Aminoethyl)-2-methoxyphenyl]-5-methyl-7-[3-(trifluoromethyl)-phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine;
- N-(2,4-Dimethoxyphenyl)-5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine;
- N-(2,5-Dimethoxyphenyl)-5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine;
- Ethyl 5-({5-methyl-7-[3-(trifluoromethyl)phenyl]imidazo[5,1-f][1,2,4]triazin-2-yl}amino)nicotinate;
- 2-{3-[(5-Methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-yl)amino]phenyl}-ethanesulfonic acid;
- 5-Methyl-7-[3-(1H-pyrazol-4-ylethynyl)phenyl]-N-(3,4,5-trimethoxyphenyl)-imidazo[5,1-f][1,2,4]triazin-2-amine;
- 3′-{5-Methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}-1,1′-biphenyl-3-carboxylic acid;
- 2-Amino-3-(3′-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo-[5,1-f][1,2,4]triazin-7-yl}-1,1′-biphenyl-4-yl)propanoic acid;
- 5-Methyl-7-[2′-(trifluoromethyl)-1,1′-biphenyl-3-yl]-N-(3,4,5-trimethoxyphenyl)-imidazo[5,1-f][1,2,4]triazin-2-amine;
- (2Z)-3-(3-{5-Methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}phenyl)-3-phenylprop-2-enamide;
- 7-(3-{[5-(Ethylsulfonyl)-2-methoxyphenyl]amino}phenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-7-(3-{[4-(1H-1,2,4-triazol-1-ylmethyl)phenyl]amino}phenyl)-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 7-(3-{[4-(1H-imidazol-1-yl)phenyl]amino}phenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 7-{3-[(3-Chloro-4-morpholin-4-ylphenyl)amino]phenyl}-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- N,N-Dimethyl-1-{3-[(3-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino] imidazo[5,1-f][1,2,4]triazin-7-yl}phenyl)amino]phenyl}-methanesulfonamide;
- 5-Methyl-7-[3-({4-[(4-methylpiperazin-1-yl)methyl]phenyl}-amino)phenyl]-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- N-Cyclopropyl-3-[(3-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}phenyl)amino]benzenesulfonamide;
- 7-(5-Bromo-2-thienyl)-5-methyl-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine;
- 7-(3-Bromo-2-thienyl)-5-methyl-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-N-[4-(methyloxy)phenyl]-7-(tetrahydro-2H-pyran-4-yl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-7-[2-(methyloxy)phenyl]-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-7-[3-(methyloxy)phenyl]-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine;
- 7-(2-Chlorophenyl)-5-methyl-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-7-(1-methyl-1H-indol-3-yl)-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-N-[4-(methyloxy)phenyl]-7-(1-phenylethyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-7-(1-methyl-1H-indol-2-yl)-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-N-[4-(methyloxy)phenyl]-7-(3-thienyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 7-(3-Furanyl)-5-methyl-N-[4-(methyloxy)phenyl]imidazo-[5,1-f][1,2,4]triazin-2-amine;
- 7-(2-Furanyl)-5-methyl-N-[4-(methyloxy)phenyl]imidazo-[5,1-f][1,2,4]triazin-2-amine;
- 7-(4-Fluorophenyl)-5-methyl-N-[4-(methyloxy)phenyl]-imidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-N-[4-(methyloxy)phenyl]-7-(2-thienyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 7-Cyclopropyl-5-methyl-N-[4-(methyloxy)phenyl]-imidazo[5,1-f][1,2,4]triazin-2-amine;
- 7-Cyclohexyl-5-methyl-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine;
- 7-(2-FluorophenylFluorophenyl)-5-methyl-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-N,7-bis[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-N-[4-(methyloxy)phenyl]-7-(phenylmethyl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 7-(3-Fluorophenyl)-5-methyl-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine;
- 7-Cyclohexyl-5-methyl-N-[3,4,5-tris(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine;
- 7-(Cyclohexylmethyl)-5-methyl-N-[4-(methyloxy)phenyl]-imidazo[5,1-f][1,2,4]triazin-2-amine;
- N-[3,4-Bis(methyloxy)phenyl]-5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine;
- N-[3,5-Bis(methyloxy)phenyl]-5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine;
- N-{4-[(5-Methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-yl)amino]phenyl}acetamide;
- 5-Methyl-N-[4-(methylthio)phenyl]-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine;
- N-(4-{[2-(Dimethylamino)ethyl]oxy}phenyl)-5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-7-phenyl-N-(4-{[2-(1-piperidinyl)ethyl]-oxy}phenyl)-imidazo[5,1-f][1,2,4]triazin-2-amine;
- N-(3-{[2-(Dimethylamino)ethyl]oxy}phenyl)-5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine;
- N-(1-Acetyl-2,3-dihydro-1H-indol-5-yl)-5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine;
- N-Cyclohexyl-5-methyl-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-7-phenyl-N-(tetrahydro-2H-pyran-4-yl)imidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-N-(4-{[2-(4-morpholinyl)ethyl]oxy}phenyl)-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-N-(3-{[2-(4-morpholinyl)ethyl]oxy}phenyl)-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-N-[4-(methyloxy)phenyl]-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-N,7-diphenylimidazo[5,1-f][1,2,4]triazin-2-amine;
- 5-Methyl-N-[3-(methyloxy)phenyl]-7-phenylimidazo[5,1-f][1,2,4]triazin-2-amine;
- and pharmaceutically acceptable salts, solvates and physiologically functional derivatives thereof.
104 more elements
37-46. (canceled)
Dependencies are inferred from the claim text.